X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .43. METAL-ION CATALYZED ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF IMINES AND MENTHYL ACRYLATE

被引：62
作者：
BARR, DA
DORRITY, MJ
GRIGG, R
HARGREAVES, S
MALONE, JF
MONTGOMERY, J
REDPATH, J
STEVENSON, P
THORNTONPETT, M
机构：
[1] UNIV LEEDS,SCH CHEM,LEEDS LS2 9JT,W YORKSHIRE,ENGLAND
[2] QUEENS UNIV BELFAST,DEPT CHEM,BELFAST BT9 5AG,ANTRIM,NORTH IRELAND
[3] ORGANON RES LABS LTD,NEWHOUSE ML1 5SH,LANARK,SCOTLAND
来源：
TETRAHEDRON | 1995年 / 51卷 / 01期
关键词：
D O I：
10.1016/0040-4020(94)00940-V
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Metallo-azomethine ylides, generated from imines by the action of amine bases in combination with LiBr or AgOAc, undergo cycloaddition with both 1R, 2S, 5R- and 1S, 2R, 5S-menthyl acrylate at room temperature to give homochiral pyrrolidines in excellent yield. The stronger the base the faster the cycloaddition and the greater the yield with: 2-t-butyl-1,1,3,3-tetramethylguanidine > DBU > NEt(3) X-Ray crystal structures of representative cycloadducts establish that the absolute configuration of the newly established pyrrolidine stereocentres is independent of the metal salt and the size of the pyrrolidineC(2)-substituent for a series of aryl and aliphatic imines.
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页码：273 / 294
页数：22
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